N-Hydroxy Amides. IV. Synthesis and Properties of a Trihydroxamic Acid Anilide as a Model for Ferrioxamines

Article abstract of DOI:10.1246/bcsj.59.2421

A trihydroxamic acid having a 6-aminohexanoyl-3-(hydroxyamino)propanoyl sequence has been synthesized in a stepwise manner, starting with glycinanilide.The trihydroxamic acid anilide bears a good structural resemblance with N-benzoyl-diferrierrioxamine B (Benzoyl-DFB).A plot of the absorbance vs. the molar ratio of iron(III) to the hydroxamate group indicates the formation of a 1:1 intramolecular iron(III) complex for the trihydroxamic acid anilide and Benzoyl-DFB.Cyclic voltammetry also shows that the iron complexes of both compounds have similar electrochemical properties.A solid iron(III) complex was obtained when the trihydroxamic ad anilide was mixed with tris(2,4-pentanedionato)iron(III) in methanol.